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It had been a long, thirsty day, and we were kicking back at Prado No. 12, a tiny bar in a flat iron building very close to the spray-soaked Malecón seawall that frames the north side of Havana.

At a nearby table was Steve, weighing the merits of the Montecristo Especial No 2 he held thoughtfully between his fingers. Steve was from Tampa, and made his living escorting Americans on limited tours into Havana. How hard was it to get a licence from U.S. authorities to do that? “It was like walking over eight miles of broken glass,” he replied. He looked around happily as the sun set over the Strait of Florida and young people drifted over to the seawall.

“You know, my government calls Cuba a terrorist state. Not Pakistan. Cuba.” A little girl skipped by, her curly ponytail tied up with red ribbons, holding tightly onto her small brother who clutched a baseball in one hand and trailed a glove in the other. Steve pulled reflectively on his cigar, blew out a smoke ring and drawled, “Do they look like terrorists to you?”

Havana is a city half in ruins, thanks to the 50 plus year old U.S. economic embargo. It shouldn’t work, but it does, and in a spectacular fashion, and with the loosening of economic policies under Raul Castro, the emergence of a new kind of Cuba is evident on its streets. Twenty-six years ago, I travelled here with a backpack and no reservations, at a time when the Russians were calling the shots. Havana seemed a dark, dour and sometimes scary place then. The 1950s era cars that chug along the eight-kilometre Malecón are still there, but other things are changing, and fast. Private businesses are popping up all over, from the old men selling leaf-wrapped maize snacks from buckets strapped to their bikes, to private taxi cabs, to neighbourhood beauty parlours and privately owned restaurants, called paladares.

If you want an insight into the lives of ordinary Cubans, stay in a casa particular. Cubans have been welcoming travellers into their homes since 1996 in casas that are strictly licensed and regulated by the government. Once you hook into that network, your accommodation problems in Havana, or anywhere else in Cuba, are over. If one casa is filled, the owners will simply pass you along to a friend, neighbour or relative. In a country where Internet access is limited, that help is essential.

We lucked out at Casa Diana, a graciously disintegrating home in Vedado, a leafy area well away from the hustle and noise of Centro Habana and the touristy old city. Casa Diana was an oasis of peace, with a cool, fern-filled patio, an interior courtyard covered by an airy mesh that filtered the noon-day heat, and elegant rooms filled with paintings, ceramics and a lifetime of memories.

Our small, comfortable room with ensuite was spotless, and our hosts spoke excellent English. Each morning Diana’s husband, Tony, who is well into his 80s, served us fresh fruit, coffee, scrambled eggs and bread.

We paid for our stay in Cuban Convertible Pesos – CUCs for short. One CUC equals about $1.06 Canadian. At 40$CUCs ($42.40) a night plus breakfast, the casa was a good deal. But like everything in Cuba, the currency can be confusing. There are two in play. Tourists convert cash into CUCs, but they can also get Cuban pesos, which is what the locals use. The trouble is, you can’t always spend the local currency in places that cater to tourists. Conversely, you might pay for a juice at a roadside stand with a CUC, and get change back in Cuban pesos. I told you it was complicated. It’s useful to have some Cuban pesos on hand for small purchases (and they make great souvenirs), but otherwise, just stick with the CUCs. Cuba’s hard enough to figure out without spending your time calculating coinage in two currencies.

One morning after breakfast, Tony pulled out the family photo album. After a brief stint as a croupier in a Batista-era casino, he joined the Havana police force and became part of their acrobatic motorcycle team. The photos show him shooting his bike through hoops of fire, or riding two abreast while more than a dozen officers hang off the bikes. Tony went on to work logistics for the Cuban military, and travelled the world – Angola, China, North Korea. We could have sat there all day listening to his stories.

But most visitors to the island don’t get a chance to look over family photo albums with local Cubans, and they don’t stay in casas. It’s very tempting and just easier to simply book into an all-inclusive resort, and enjoy a beach vacation. Many tourists are perfectly happy taking escorted day trips into Havana from resorts in Varadero, about two hours away. They are deposited directly on the doorsteps of the meticulously restored squares of Old Havana, and shepherded along the Calle Mercaderes, where the pink, yellow and green pastels of the architectural jewels that line the street enchant the visitor. Against all the economic odds, Havana has managed to make the restoration of the area a priority and is doing an internationally acclaimed job of preserving the city’s history and architecture, and employing hundreds of people in the process.

But it’s perfectly safe to wander around the city without a guide, although the usual cautions apply: wear a money belt (and it’s a cash economy so you’ll need lots of those CUCs), watch your day pack, and be prepared to bargain the price of a taxi fare. Polite and repeated “no, gracias” gets rid of any persistent touts. The biggest risk you run is dodging traffic. Watch out for zippy little three wheeled coco-taxis, which look for all the world like hollowed out yellow coconuts, hence the name. Add in broken down Ladas from the Russian days, and chrome-laden and fin-tailed classic American cars from the ’50s all jostling for space and fares as they careen along Havana’s disintegrating roads, and you’ll need to keep your wits about you.

The Malecón seawall is a magnet at sunset. The light turns the crumbling buildings lining the harbour a rich, lemony-custard yellow, and Habaneros head there to play music, hang out, and plan the evening’s fun. After our legs gave out, we hailed a coco-taxi and hurtled off to the Hotel Nacional for a drink, where you can watch all the action from the terrasse. The Nacional’s the place where mobsters Lansky Meyers and Lucky Luciano hung out in pre-revolution days, and where the opponents of former dictator Fulgencio Batista were gunned down in the lobby. Today, you get to soak up all that history and a lot more for the price of a drink.

One day, tiring of the noise and chaos of the streets, we ducked into the lobby of the opulent 5 star Parque Central Hotel. We’d been told that for a few CUCs anyone could use their rooftop swimming pool. “No, madam,” said the concierge dismissively, “The pool is for hotel guests only.” He turned his back. We made a break for the elevators. Topside, we ordered up a mojito, enjoyed the band and were treated to a poolside fashion show. With the Capitolia glistening white in the background, doe-eyed male and female models loped alongside the azure pool, wearing the latest in designer wear from Cuba as they struck provocative poses.

Ah, well. Viva la revolutión!

Later that evening, we set out for Havana’s famed jazz nightclub La Zorra y El Cuervo. Beefy, red-coated bouncers who managed to look both welcoming and threatening pulled open the door of a giant red telephone box, and down we went. Show time was 11 p.m., and the CUC$10 ($10.58) charge covered a couple of drinks. To our delight, Yasek Manzano took the stage. He’s one of the most exciting young jazz trumpet players to come out of Cuba in the last decade. Manzano sent notes spinning into orbit one moment, and made his trumpet weep like a baby the next, playing original compositions and a version of the old standard Blame It on My Youth that had me in tears. Definitely time to go home. The nice bouncers at the door made sure we got safely into a cab for another bone-rattling ride back to the casa.

The next day, we made tracks for the eye-popping Callejón de Hamel, a short, narrow street where every wall is covered with outrageously vibrant murals and the surrounding streets reverberate with frenetic rumba music. We wandered the back alleys of Centro Habana, making friends with a trio of little girls working on their ABCs with a broken pencil and a scrap of paper. We took the local ferry across the harbour to Casa Blanca and were rewarded with a stunning view back at this sprawling city of two million people.

Cuba has a well-deserved reputation for spectacularly bad food, but that’s largely based on what’s offered at resorts on the Atlantic coast, where resort chains are doing their best to serve hundreds of people in massive meal halls. Eating in Havana was an eye-opener. From tiny neighbourhood cafés like El Bosquecito in Habana Veija , where CUC$4 ($4.25) gets you a delicious omelette and salad with cheese, to the classy, outdoor grill El Idilio in Vedado, where we dined on mouth watering paella, with appetizers and wine, for CUC$50 ($52.89), Havana has it all. With ordinary Cubans facing daily food shortages and rationing, that abundance is another Cuban contradiction that gives you pause.

The paladar La Guarida is by far the coolest place to eat in Havana. Its’ reputation exploded in 1993 when the movie Fresa y Chocolate (Strawberries and Chocolate) was shot there. The film tells the story of a love affair between two young men, a free-spirited artist and a doctrinaire communist. The movie was an international hit and it put La Guarida on the culinary map. A couple of swashbuckling reviews in The Guardian and The New York Times didn’t hurt, either, according to Lonely Planet.

Getting there was half the adventure. We piled into Tony’s Lada, but even he got lost in the darkened maze of Centro Habana. We bumped over potholes, and swerved around dogs picking over spilled garbage as young people gathered on street corners to argue and flirt. We finally pulled up in front of a three-storey, spectacularly dilapidated mansion-turned-tenement building. The two cheerful youths manning the ornately carved double wooden door took one look at us and jerked their thumbs towards the stairs.

We stepped into a dimly lit foyer dominated by a sweeping marble staircase, broken statuary, and a quotation from Fidel carved into the wall. The first floor revealed a vast colonnaded room open to the night air, and piles of construction material and rubbish in one corner. Down the corridor, lights spilled from rooms and explosions of laughter echoed through the stairwells.

We reached the second landing, pushed open a door, and fell into another world. Movie prints and framed photographs of ballet dancers covered honey-coloured walls, and glittering chandeliers hung from 15-foot ceilings. We were shown to our table on a tiny balcony, and enjoyed one of the best meals we’ve had anywhere. The service was exquisite, as was the food. We opted for spinach crêpes stuffed with chicken, fungi sauce and beef vinaigrette, swordfish and vanilla with seafood sauce, and for dessert, guava mousse with orange coulis and lemon tart with almonds, all washed down with a decent Chilean cabernet sauvignon. Dinner for two, with tip, was about CUC$100 ($105.77).

As darkness fell, we lingered over the wine, and tried to make sense of the contradictions that define this country. We know the meal we just ate cost three times as much as what many Cubans earn in a month – even IF their education and health care is free and they pay next to nothing for utilities. We know the Cuban blogger Yoani Sánchez has an international reputation for her sharply critical views of the current government and her descriptions of the hardship of daily life in Cuba. Her blog, Generation Y, evades censorship because she emails it to friends outside the country who then publish it on line. We’re aware that sex tourism is a problem here, and yes, we realize Canadians like us risk addiction to a romanticized idea of what Cuba is, or might be.

But there’s something very special about the place, because of its past, and the way it manages the present. Who knows what the future holds?

We raised a glass and toasted this stubborn and boisterous city and the irrepressible people who call it home.

IF YOU GO

Flights: Air Canada offers regular service to Havana from Montreal with a stopover in Toronto, starting at $664.80 return, all taxes in. Cubana, Cuba’s national airline, offers direct flights to Havana from Montreal, and gets mixed reviews for service and delays, starting at around $568.

Where to stay: For a full listing of casas throughout Cuba, check out cubacasas.net.

Money: Change your money on arrival at the Jose Marti Airport near the luggage carousel or outside the doors where families wait, at your hotel, or at any bank. The tourist currency is the CUC — the Cuban Convertible Peso. Once in Havana, you can also exchange Canadian dollars for CUCs at a Casa de Cambio. You can use some ATMs to get CUCs with a Visa or MasterCard, but NOT if those cards were issued by U.S. banks. U.S. dollars are not accepted in Cuba.

Deborah Woolway is a freelance journalist based in Dartmouth, N.S.

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